US2784138A - Fungicidal compositions of nu-arylhydroxyarylmethylamines - Google Patents
Fungicidal compositions of nu-arylhydroxyarylmethylamines Download PDFInfo
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- US2784138A US2784138A US413718A US41371854A US2784138A US 2784138 A US2784138 A US 2784138A US 413718 A US413718 A US 413718A US 41371854 A US41371854 A US 41371854A US 2784138 A US2784138 A US 2784138A
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- Prior art keywords
- spores
- fungicidal
- concentration
- nitro
- phenols
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- 230000000855 fungicidal effect Effects 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 title claims description 9
- 239000004615 ingredient Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 4
- 230000035784 germination Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 231100000208 phytotoxic Toxicity 0.000 description 4
- 230000000885 phytotoxic effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- AUESJGZPPPVYJZ-UHFFFAOYSA-N 2-(chloromethyl)phenol Chemical class OC1=CC=CC=C1CCl AUESJGZPPPVYJZ-UHFFFAOYSA-N 0.000 description 3
- -1 amine compound Chemical class 0.000 description 3
- 150000004982 aromatic amines Chemical group 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000000266 injurious effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- LILWDQKYRRCSOS-UHFFFAOYSA-N 2,3-bis(chloromethyl)phenol Chemical class OC1=CC=CC(CCl)=C1CCl LILWDQKYRRCSOS-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- GAKLFAZBKQGUBO-UHFFFAOYSA-N 2-methyl-3-nitrophenol Chemical class CC1=C(O)C=CC=C1[N+]([O-])=O GAKLFAZBKQGUBO-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical group O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229950002705 arsanilic acid Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- KPRZOPQOBJRYSW-UHFFFAOYSA-N o-hydroxybenzylamine Natural products NCC1=CC=CC=C1O KPRZOPQOBJRYSW-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 150000002931 p-cresols Chemical class 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/74—Aromatic compounds
Definitions
- Phenol and its substitution products for instance cresol, trior pentachlorophenol as well as dinitro-o-cresol, are known to have marked fungicidal properties.
- the general. application of these products in the control of plant diseases ishandicapped by their, mostly considerable, injurious (phytotoxic) effects on plants.
- the application of these phenols therefore, is limited substantially to the preservation of wood or, if applied in the control of plant diseases, to the seasons in which the plants have no green parts.
- the fungicidal propertiesof phenols and its substitution products are preserved if they contain as a Weakly basic group an aromatic amine residue attached to the phenol radical via a methylenebridge.
- yflfhe aryl pent may be substituted for instance by alkyl, halogen or nitro groups.
- the aromatic radicals may belong to the benzene series or to any other aromatioring system.
- the nitrogen atom of the compounds may be secondary or tertiary.
- N-aryl-hydroxy-arylmethylamines are the suppression of the strong skin-irritating properties which are otherwise characteristic of phenols. This is presumably due to an internal salt formation between the phenol and the amine compound.
- water-soluble salts of the N-aryl-hydroXy-arylrnethylamines since these salts are especially active and easy to handle.
- the phenolic group and especially the amino group can be used.
- the N-aryl-hydroxyarylmethylamines are preferably prepared via the corresponding chloromethylphenols if the starting products are phenols the reactivity of which is reduced to such an extent that a chloromethyl compound can be produced therefrom. This is the case for instance with oor p-nitrophenol or the corresponding nitrocresols or p-cresols, furthermore with dinitrophenols, nitro-oor -p-chlorophenol, with dichlorophenol and,
- a chloromethyl group can be introduced in-m-position to the hydroxyl group.
- These and the aforesaid-phenols are capable of yielding.
- di-(chloromethyl)-phenols and pan further be reacted with two ,rnols of the same or two different amines.
- the methylol compounds which are more easily obtainable may be reacted with the amines at elevated temperatures to form the corresponding N-aryl-hydroXy-arylmethylamines and water.
- the reaction of chloromethyl phenols with the arcmatic amines can be accomplished by slightly heating the components; it is advantageous to apply the aromatic amines in a large excess in order to avoid theformation
- the fungicidalpropertiesof the products according to the invention are sometimes enhanced by esterifying the N-aryl-hydroxyarylmethylamines at the phenolic hydroxyl group by conventional methods. This esterification step is preferably carried out before or after chloromethylation, i. e. prior to the reaction with the aromatic amines.
- the invention is, further illustrated byv the following examples without beingrestricted thereto.
- Example 1 N 4-chlorophenyl) -N-5-nitro-2-hydroxybenzylaminechlorohydrate (M.-P.: 158". C with decomposition after recrystallizing from methanol) is active against Phytophtora infestans and Peronospora on .theplant and. not phytotoxic. When tested with spores in a concentration of 0.0005%, of the spores no longer germinate; 50% of the spores lose their germination capability if the product is applied in a concentration of 0.00025
- Example 2 When testing N-(2 -nitrophenyl)eN-5-nitro-2-hydroxybenzylamine (M. P.:,1 68 C.
- Example 3 N (3 nitrophenyl)-N-5-nitro-2-hydroxybenzylamine (M. P.: 179 C.; yellow powder) is active against Phyt. and Per. on the plant and not phytotoxic. When tested with spores in a concentration of 0.0005 80% of the spores no longer germinate; 50% of the spores lose their germination capability if the product is applied in a concentration of 0.00025%.
- Example 4 N (4-nitrophenyl) N-5-nitro-Z-hydroxybenzylamine (M. P.: 192 C.) is not phytotoxic. When tested with spores in a concentration of 0.0005%, 80% of the spores no longer germinate; 55% of the spores lose their germination capability if the product is applied in a concentration of 0.00025
- Example 5 N '(2,4-dichlorophenyl)-N-5-nitro 2 hydroxybenzylamine (M. P.: 148 C.) is present in the form of yellow crystals after recrystallizing from xylene. When tested with spores in a concentration of 0.0005%, 90% of the spores no longer germinate.
- Example 6 When testing N-(-nitro-2-hydroxybenzyl)-arsanilic acid (M. P.: 245 C.) with spores in a concentration of 0.0005%, 45% of the spores no longer germinate.
- Example 7 When testing N-a-(piridyl-N-5-chloro-3-nitro-2hydroxybenzylamine (M. P.: 228 C.) with spores in a concentration of 0.0005%, 26% of the spores no longer germinate.
- Example 8 When testing N-a-piridyl-N-5-nitro-3methyl-2-hydroxybenzylamine (M. P.: 200 C.) with spores in a concentration of 0.0005%, 33% of the spores no longer germinate.
- Example 9 When testing N (4-chl'orophenyl)-N-3 ,5-dichloro-2-hydroxybenzylamine (M. P.: 114 C.) with spores in a concentration of 0.0005 70% of the spores no longer germinate.
- a fungicidal composition containing as an active fungicidal ingredient a substance of the formula CHr-NH-Ar in which R is a member selected from the group consisting of N02 and Cl, and a carrier,
- a fungicidal composition containing as an fungicidal ingredient a substance of the formula and a carrier.
- a fungicidal composition containing as an fungicidal ingredient a substance of the formula OzN- GHa-NH 0H Cl and a carrier.
- a fungicidal composition containing as an active fungicidal ingredient a substance of the formula O2N OHrNH- and a carrier.
- a fungicidal composition containing as an fungicidal ingredient a substance of the formula and a carrier.
- a fungicidal composition containing as an fungicidal ingredient a substance of the formula and a carrier.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
radicals of the phenol and the an ine compo United States Patent FUNGICIDAL COMPOSITIONS F N-ARYL- HYDROXYARYLMETHYLAMIN ES Richard Wegler, Leverkusen, and. Ferdinand Grewe and Erik Regel, Koln-Flittard, Germany, assignors .to.Farbenfabriken Bayer Aktiengesellschaft, Leverkusen, Germany, a corporation of Germany N0 Drawing. Application March 2, 1954, Serial No. 413,718
Claims priority, application Germany March 7, 1953 7 Claims. (Cl. 167-31) @qm-u H-Ar a wherein Rrepresents hydrogen, a loweralkyl, halogen or nitro, group, Ar stands for a halo-.onnitrmsubstituted phenyl radical or an arsenic acid group or an alpha-pyridyl radical which have been found to be efiective fungicides.
Phenol and its substitution products, for instance cresol, trior pentachlorophenol as well as dinitro-o-cresol, are known to have marked fungicidal properties. The general. application of these products in the control of plant diseases ishandicapped by their, mostly considerable, injurious (phytotoxic) effects on plants. The application of these phenols, therefore, is limited substantially to the preservation of wood or, if applied in the control of plant diseases, to the seasons in which the plants have no green parts.
In accordance with the present invention it has been found that the fungicidal propertiesof phenols and its substitution products are preserved if they contain as a Weakly basic group an aromatic amine residue attached to the phenol radical via a methylenebridge. yflfhe aryl pentmay be substituted for instance by alkyl, halogen or nitro groups. The aromatic radicals may belong to the benzene series or to any other aromatioring system. The nitrogen atom of the compounds may be secondary or tertiary. By introducing the amine residue in accordance with the invention the injurious action of the above phenols on leaves is very surprisingly either eliminated completely or at least reduced to such an extent that may be employed as fungicides without any risk during the whole year. In accordance with the invention another advantage of the N-aryl-hydroxy-arylmethylamines is the suppression of the strong skin-irritating properties which are otherwise characteristic of phenols. This is presumably due to an internal salt formation between the phenol and the amine compound. In many cases it is of advantage to employ the water-soluble salts of the N-aryl-hydroXy-arylrnethylamines since these salts are especially active and easy to handle. For the preparation of salts the phenolic group and especially the amino group can be used.
The N-aryl-hydroxyarylmethylamines are preferably prepared via the corresponding chloromethylphenols if the starting products are phenols the reactivity of which is reduced to such an extent that a chloromethyl compound can be produced therefrom. This is the case for instance with oor p-nitrophenol or the corresponding nitrocresols or p-cresols, furthermore with dinitrophenols, nitro-oor -p-chlorophenol, with dichlorophenol and,
.of by-products.
quite generally, with compounds containing at least two substituents in oand. p-position or in both o-positions or a substituent of the second order in oor p-position.
Inphenols carrying substituents in p-position and both oapositions, for instance .mesitol and trichlorophenol, a chloromethyl group can be introduced in-m-position to the hydroxyl group. These and the aforesaid-phenols are capable of yielding. di-(chloromethyl)-phenols and pan further be reacted with two ,rnols of the same or two different amines. In the case of particularly reactive phenols, instead of the chloromethylphenols the methylol compounds which are more easily obtainable may be reacted with the amines at elevated temperatures to form the corresponding N-aryl-hydroXy-arylmethylamines and water.
The reaction of chloromethyl phenols with the arcmatic amines can be accomplished by slightly heating the components; it is advantageous to apply the aromatic amines in a large excess in order to avoid theformation The fungicidalpropertiesof the products according to the invention are sometimes enhanced by esterifying the N-aryl-hydroxyarylmethylamines at the phenolic hydroxyl group by conventional methods. This esterification step is preferably carried out before or after chloromethylation, i. e. prior to the reaction with the aromatic amines.
The invention is, further illustrated byv the following examples without beingrestricted thereto.
Example 1 N 4-chlorophenyl) -N-5-nitro-2-hydroxybenzylaminechlorohydrate (M.-P.: 158". C with decomposition after recrystallizing from methanol) is active against Phytophtora infestans and Peronospora on .theplant and. not phytotoxic. When tested with spores in a concentration of 0.0005%, of the spores no longer germinate; 50% of the spores lose their germination capability if the product is applied in a concentration of 0.00025 Example 2 When testing N-(2 -nitrophenyl)eN-5-nitro-2-hydroxybenzylamine (M. P.:,1 68 C. after recrystallizing from Xylene; red powder) with spores in a concentration of 0.0005 of the spores no longer germinate; 65% of the spores lose their germination capability if the product is applied in a concentration of 0.00025%.
Example 3 N (3 nitrophenyl)-N-5-nitro-2-hydroxybenzylamine (M. P.: 179 C.; yellow powder) is active against Phyt. and Per. on the plant and not phytotoxic. When tested with spores in a concentration of 0.0005 80% of the spores no longer germinate; 50% of the spores lose their germination capability if the product is applied in a concentration of 0.00025%.
Example 4 N (4-nitrophenyl) N-5-nitro-Z-hydroxybenzylamine (M. P.: 192 C.) is not phytotoxic. When tested with spores in a concentration of 0.0005%, 80% of the spores no longer germinate; 55% of the spores lose their germination capability if the product is applied in a concentration of 0.00025 Example 5 N '(2,4-dichlorophenyl)-N-5-nitro 2 hydroxybenzylamine (M. P.: 148 C.) is present in the form of yellow crystals after recrystallizing from xylene. When tested with spores in a concentration of 0.0005%, 90% of the spores no longer germinate.
Example 6 When testing N-(-nitro-2-hydroxybenzyl)-arsanilic acid (M. P.: 245 C.) with spores in a concentration of 0.0005%, 45% of the spores no longer germinate.
Example 7 When testing N-a-(piridyl-N-5-chloro-3-nitro-2hydroxybenzylamine (M. P.: 228 C.) with spores in a concentration of 0.0005%, 26% of the spores no longer germinate.
Example 8 When testing N-a-piridyl-N-5-nitro-3methyl-2-hydroxybenzylamine (M. P.: 200 C.) with spores in a concentration of 0.0005%, 33% of the spores no longer germinate.
Example 9 When testing N (4-chl'orophenyl)-N-3 ,5-dichloro-2-hydroxybenzylamine (M. P.: 114 C.) with spores in a concentration of 0.0005 70% of the spores no longer germinate.
We claim: 1. A fungicidal composition containing as an active fungicidal ingredient a substance of the formula CHr-NH-Ar in which R is a member selected from the group consisting of N02 and Cl, and a carrier,
3. A fungicidal composition containing as an fungicidal ingredient a substance of the formula and a carrier.
4. A fungicidal composition containing as an fungicidal ingredient a substance of the formula OzN- GHa-NH 0H Cl and a carrier.
5. A fungicidal composition containing as an active fungicidal ingredient a substance of the formula O2N OHrNH- and a carrier.
6. A fungicidal composition containing as an fungicidal ingredient a substance of the formula and a carrier.
7. A fungicidal composition containing as an fungicidal ingredient a substance of the formula and a carrier.
active active active active References Cited in the file of this patent UNITED STATES PATENTS Britton et a1 Apr. 18, 1939 OBrien et a1. June 30, 1953
Claims (1)
1. A FUNGICIDAL COMPOSITION CONTAINING AS AN ACTIVE FUNGICIDAL INGREDIENT A SUBSTANCE OF THE FORMULA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2784138X | 1953-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2784138A true US2784138A (en) | 1957-03-05 |
Family
ID=7998307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US413718A Expired - Lifetime US2784138A (en) | 1953-03-07 | 1954-03-02 | Fungicidal compositions of nu-arylhydroxyarylmethylamines |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2784138A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2981619A (en) * | 1957-04-05 | 1961-04-25 | Dow Chemical Co | Method of inhibiting plant growth |
| US2989391A (en) * | 1957-04-05 | 1961-06-20 | Dow Chemical Co | Method for modifying the growth characteristics of plants |
| US3173952A (en) * | 1959-12-24 | 1965-03-16 | Monsanto Co | Tris-(3, 5-dialkyl-4-hydroxybenzyl) amines |
| US3227759A (en) * | 1962-07-10 | 1966-01-04 | Velsicol Chemical Corp | N-(substituted phenyl)-aralkyl amines |
| US3227758A (en) * | 1962-07-10 | 1966-01-04 | Velsicol Chemical Corp | Phenalkylamines |
| US3227757A (en) * | 1962-07-10 | 1966-01-04 | Velsicol Chemical Corp | N (substituted phenyl)-aralkylamines |
| EP0000816A1 (en) * | 1977-08-06 | 1979-02-21 | Beecham Group Plc | Substituted amino-pyridine derivatives, processes for their preparation and pharmaceutical compositions containing them |
| EP0081782A1 (en) * | 1981-12-14 | 1983-06-22 | Merck & Co. Inc. | Hydroxybenzylamino-aryl compounds, process for preparing and pharmaceutical compositions containing the same |
| US4578390A (en) * | 1981-12-14 | 1986-03-25 | Merck & Co., Inc. | Hydroxybenzylamino derivatives as anti-inflammatory agents |
| US5021458A (en) * | 1984-06-09 | 1991-06-04 | Kaken Pharmaceutical Co., Ltd. | Amine derivatives and fungicides containing the same |
| CN111971271A (en) * | 2018-01-09 | 2020-11-20 | 香港理工大学 | Compound with antibacterial activity |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2155356A (en) * | 1937-06-17 | 1939-04-18 | Dow Chemical Co | N-substituted-2-amino nitro-phenols |
| US2643965A (en) * | 1951-11-02 | 1953-06-30 | Us Rubber Co | New chemicals and fungicidal compositions containing same |
-
1954
- 1954-03-02 US US413718A patent/US2784138A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2155356A (en) * | 1937-06-17 | 1939-04-18 | Dow Chemical Co | N-substituted-2-amino nitro-phenols |
| US2643965A (en) * | 1951-11-02 | 1953-06-30 | Us Rubber Co | New chemicals and fungicidal compositions containing same |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2981619A (en) * | 1957-04-05 | 1961-04-25 | Dow Chemical Co | Method of inhibiting plant growth |
| US2989391A (en) * | 1957-04-05 | 1961-06-20 | Dow Chemical Co | Method for modifying the growth characteristics of plants |
| US3173952A (en) * | 1959-12-24 | 1965-03-16 | Monsanto Co | Tris-(3, 5-dialkyl-4-hydroxybenzyl) amines |
| US3227759A (en) * | 1962-07-10 | 1966-01-04 | Velsicol Chemical Corp | N-(substituted phenyl)-aralkyl amines |
| US3227758A (en) * | 1962-07-10 | 1966-01-04 | Velsicol Chemical Corp | Phenalkylamines |
| US3227757A (en) * | 1962-07-10 | 1966-01-04 | Velsicol Chemical Corp | N (substituted phenyl)-aralkylamines |
| EP0000816A1 (en) * | 1977-08-06 | 1979-02-21 | Beecham Group Plc | Substituted amino-pyridine derivatives, processes for their preparation and pharmaceutical compositions containing them |
| EP0081782A1 (en) * | 1981-12-14 | 1983-06-22 | Merck & Co. Inc. | Hydroxybenzylamino-aryl compounds, process for preparing and pharmaceutical compositions containing the same |
| US4578390A (en) * | 1981-12-14 | 1986-03-25 | Merck & Co., Inc. | Hydroxybenzylamino derivatives as anti-inflammatory agents |
| US5021458A (en) * | 1984-06-09 | 1991-06-04 | Kaken Pharmaceutical Co., Ltd. | Amine derivatives and fungicides containing the same |
| CN111971271A (en) * | 2018-01-09 | 2020-11-20 | 香港理工大学 | Compound with antibacterial activity |
| JP2021510143A (en) * | 2018-01-09 | 2021-04-15 | ザ ホンコン ポリテクニック ユニバーシティ | Compound with antibacterial activity |
| EP3737664A4 (en) * | 2018-01-09 | 2021-12-01 | The Hong Kong Polytechnic University | Compounds with antimicrobial activity |
| US11479529B2 (en) | 2018-01-09 | 2022-10-25 | The Hong Kong Polytechnic University | Compounds with antimicrobial activity |
| CN111971271B (en) * | 2018-01-09 | 2023-10-10 | 香港理工大学 | Compound with antibacterial activity |
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